Some movie posters for this film featured a long text preamble that read: "Haven't you ever done something in your life you wish you could do over again... and this time do it right! After fourteen years, Jack finally has a chance to replay the worst moment of his life. But first, he has to convince Reno that history won't repeat itself".

The football game at the high point of the film was shot at the Moorpark Memorial Union High School football field, just before the school moved to the Tierra Rejada Road location. The field was located at 280 Casey Road, on a hill overlooking the City of Moorpark. During the filming, in the wee hours of the morning, the temperature dropped to below freezing. The field was destroyed in the filming and the studio paid to have it re-seeded and re-landscaped.

Kirk Cameron plays Teddy Hightower, Reno and Gigi's son. Tracey Gold plays an unnamed friend of Jack and Holly's daughter Jaki Dundee. By the time this movie was released, Cameron and Gold were playing brother and sister in the television sitcom Growing Pains (1985).

Though Hightower and Dundee's alma mater is casually referred to by the characters as "Taft," the logos, signage, and lettermen's jackets in the film identify it as Midway Union High School. Early in the film, Elly Dundee (Holly Palance) complains to her husband Jack (Robin Williams) that she is "sick of having a doorbell that plays the Taft Midway Union High School Alma Mater."

Spoilers

The trivia item below may give away important plot points.

The film's title can be interpreted as being a reference to the opening line of Charles Dickens' "A Tale of Two Cities", "It was the best of times, it was the worst of times", as the film is about "the worst of times" (the loss of a football match) and "the best of times" (winning a replay rematch about a decade later).